Heterocyclylalkyl esters of 2-imidazolinonenicotinic acids

ABSTRACT

Novel heterocyclylalkyl esters of 2-imidazolinonenicotinic acids of formula I below have good selective herbicidal properties pre- and postemergence and also influence or inhibit plant growth. 
     The novel esters have the formula I ##STR1## wherein A is a straight chain or branched C 1  -C 4  alkylene bridge, X and Y are each independently of the other hydrogen, C 1  -C 3  alkyl, C 1  -C 3  haloalkyl, C 1  -C 3  alkoxy, C 1  -C 3  haloalkoxy or halogen, or X and Y together form the butadiene bridge, which may be substituted by halogen, cyano or C 1  -C 4  alkyl, and 
     Het is a 5- or 6-membered heterocycle which contains one to three nitrogen atoms and/or one oxygen or sulfur atom and which may further contain one or two carbonyl groups, which heterocycle may also be fused to benzene rings and/or substituted by halogen, C 1  -C 3  alkyl, C 1  -C 3  haloalkyl, C 1  -C 3  alkoxy, C 1  -C 3  haloalkoxy, nitro, amino, C 1  -C 3  alkylamino or di(C 1  -C 3 )alkylamino.

This is a divisional of application Ser. No. 902,805, filed on Sept. 2,1986, now U.S. Pat. No. 4,741,763, issued 5-3-88.

The present invention relates to novel herbicidal and plant growthregulating heterocyclylalkyl esters of 2-imidazolinonenicotinic acids,as well as to the preparation of these novel compounds. The inventionalso relates to compositions containing the novel2-imidazolinonenicotinic acid esters, and to methods of using them forselectively controlling weeds or for regulating plant growth.

The novel heterocyclylalkyl esters of 2-imidazolinonenicotinic acidshave the formula I ##STR2## wherein A is a straight chain or branched C₁-C₄ alkylene bridge,

X and Y are each independently of the other hydrogen, C₁ -C₃ alkyl, C₁-C₃ haloalkyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkoxy or halogen, or X and Ytogether form the butadiene bridge CH═CH--CH═CH, which may besubstituted by halogen, cyano or C₁ -C₄ alkyl, and

Het is a 5- or 6-membered heterocycle which contains one to threenitrogen atoms and/or one oxygen or sulfur atom and which may furthercontain one or two carbonyl groups, which heterocycle may also be fusedto benzene rings and/or substituted by halogen, C₁ -C₃ alkyl, C₁ -C₃haloalkyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkoxy, nitro, amino, C₁ -C₃alkylamino or di(C₁ -C₃)alkylamino, or Het is the2-(4,5-dihydro-3-methylthio-6-tert-butyl-1,3,4-triazin-5-on-2-ylhydrazineoxime)furfur-5yl radical, with the proviso that Het may not be theunsubstituted furyl radical.

In the above definitions, the alkyl and alkylene groups may be straightchain or branched, e.g. methyl, methylene, ethyl, ethylene, propyl,propylene, isopropyl, 1- or 2-methylethylene, butyl, butylene,sec-butyl, 1-methylpropylene, isobutyl, 2-methylpropylene, tert-butyl,2,2-dimethethylene and 1,2-dimethylethylene.

Halogen is fluoride, chlorine, bromine or iodine.

The heterocycles defined under Het comprise e.g. pyrrole, pyrrolidine,pyrrolidinone, pyrrolinone, pyrrolinedione, pyridine, pyridinone,pyridinedione, piperidine, piperidinone, imidazole, imidazolinone,pyrazole, pyrazolone, piperazine, diazine, diazinone, piperazinone,triazole, triazolone, triazine, triazinone, benzazole, indole,quinoline, quinolinone, benzodiazole, benzodiazolone, furfuryl,tetrahydrofuran, pyran, oxazole, oxadiazole, morpholine, thiophene,thiazole, thiadiazole and thiomorpholine.

The proviso that Het is not furan is applicable.

These rings may be unsubstituted or substituted by halogen, C₁ -C₃-alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkoxy, nitro,amino, C₁ -C₃ alkylamino or di(C₁ -C₃)alkylamino.

The preparation of such compounds can be represented by the followingscheme: ##STR3##

The process of the present invention for the preparation ofimidazolinone compounds of formula I comprises reacting a compound offormula IIa or IIb ##STR4## in which formulae X and Y are as defined forformula I, with an alkanol of formula III

    HO-A-Het                                                   (III)

wherein A and Het are as defined for formula I, in an inert organicsolvent or diluent and in the presence of a base.

Suitable solvents for these reactions are substantially anhydroushydrocarbons, ethers or ketones, e.g. benzene, toluene, xylene, hexane,cyclohexane, diisopropyl ether, tetrahydrofuran and dioxane. Examples ofsuitable bases are sodium hydride, 1,8-diazabicyclo[5.4.0]undec-7-eneand triethylamine.

These reactions are carried out in the temperature range from 0° to 200°C., generally at the boiling point of the reaction mixture.

The starting materials of formula IIa are known or they can be preparedby known methods, e.g. in accordance with published European patentapplication No. 41 623 by condensing, under basic conditions, anN-(α-isopropyl-α-methylacetamido)-2,3-pyridinecarboximide according tothe following scheme: ##STR5## A pyridine-2,3-dicarboxylic acidα-isopropyl-α-methylacetonitrile of formula IV can be prepared in simplemanner by condensing an unsaturated hydrazone with a 2-chloro- or2-bromo-N-(α-isopropyl-α-methacetonitrile)maleimide in accordance withthe following scheme: ##STR6## in which formulae each of R' and R" ishydrogen or C₁ -C₄ alkyl, Hal is chlorine or bromine, and X and Y are asdefined for formula I.

The starting materials of formula IIb are obtained by converting theabove N-(α-isopropyl-α-methylacetamido)-2,3-pyridinecarboximide, in thepresence of a base such as sodium hydroxide solution, into the2-(4-isopropyl-4-methyl-5-ioximidazolidine)nicotinic acid derivative##STR7## which is converted into the starting material of formula IIb(2-isopropyl-2-methyl-3H-imidazol[1',2':1,2]pyrrolo[3,4-b]pyridine-3,5-dione)by treatment with a condensing agent in an inert organic solvent, withthe loss of a water molecular. Such nicotinic acid esters and thepreparation thereof are described in published European patentapplication No. 41 623.

Examples of suitable condensing agents for this cyclisation are e.g. amolar amount of a strong acid, e.g. concentric sulfuric acid, or of ananhydride, or a water absorbing reagent such as cyclohexanecarbodiimide,thionyl chloride or phosgene in the presence of a small amount ofdimethylformamide. Condensation can also be effected by boiling thereaction mixture in a water separator.

If the reactions can not be carried out at room temperature, then theyare carried out in the temperature range from 0° C. to 200° C., i.e. thereaction mixture is heated--if necessary--to its boiling point andcooled--if necessary--with ice/water or ice/brine.

Suitable bases for these reactions are in particular inorganic basessuch as sodium hydroxide, sodium carbonate, sodium hydride, calciumhydroxide, calcium carbonate, potassium hydroxide, potassium carbonate,ammonia and tertiary organic bases such as triethylamine.

Suitable solvents are e.g. polar, aprotic solvents which can be used bythemselves or in mixtures consisting of at least two solvents.

Among the novel esters of formula I, very active nicotinic acid estersare those wherein

A is a methylene or ethylene bridge which may be substituted by methyl,

X is hydrogen or C₁ -C₃ alkyl,

Y is hydrogen and

Het is as defined above, and also those wherein

A is the methylene, ethyl-1-ene or ethyl-2-ene bridge,

X is hydrogen or C₁ -C₃ alkyl,

Y is hydrogen and

Het is an unsaturated 5- or 6-membered heterocycle which contains one tothree nitrogen atoms and which may further contain one or two carbonylgroups, which heterocycle may also be fused to benzene rings andsubstituted by methyl.

In particular the following compounds are very effective:

4-pyridylmethyl2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-5-methylnicotinate;

indolylethyl5-ethyl-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)nicotinate;

indolylethyl2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-5-methylnicotinate;

pyridin-2-ylethyl5-ethyl-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)nicotinate;

isoindol-2-ylethyl5-ethyl-2-(5-isopropyl-5-methyl-4-oxo-4,5-di-hydroimidazolin-2-yl)nicotinate;

pyridin-2-ylmethyl5-ethyl-2-(5-isopropyl-5-methyl-4-oxo-4,5-di-hydroimidazolin-2-yl)nicotinate;pyridin-3-ylmethyl5-ethyl-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)nicotinate;

pyridin-4-ylmethyl5-ethyl-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)nicotinate;

pyridin-2-ylmethyl2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-5-methylnicotinate;

pyridin-3-ylmethyl2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-5-methylnicotinate;

pyridin-2-ylethyl2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)nicotinate and

pyridin-2-ylethyl2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-5-methylnicotinate.

The invention relates to all diasetereomeric and enantiomeric isomers ofthe compounds of formula I.

The compounds of formula I are usually successfully applied atconcentrations of 0.05 to 4 kg/ha, in particular 0.1 to 1 kg/ha.

When used at low rates of application, the compounds of formula I havegood selective growth inhibiting and selective herbicidal propertieswhich make them most suitable for use in crops of useful plants,preferably in cereals, cotton, soybeans, maize and rice. In some casesdamage is also caused to weeds which have only been controlled up to nowwith total herbicides.

The mode of action of these compounds is unusual. Many aretranslocatable, i.e. they are absorbed by the plant and transported toother parts of it where they then exert their action. Thus, for example,it is possible to damage perennial weeds to the roots by surfacetreatment. Compared with other herbicides and growth regulators, thenovel compounds of formula I are effective even when used at very lowrates of application.

The compounds of formula I have in addition pronounced plant growthinhibiting properties. The growth of both monocots and dicots isinhibited.

Thus, for example, the compounds of formula I selectively inhibit thegrowth of leguminosae which are frequently planted as cover crops intropical regions, so that, while soil erosion between cultivated plantsis prevented, the cover crops cannot compete with the cultivated plants.

Inhibition of the vegetative growth of many cultivated plants permitsmore plants to be sown in a crop area, so that a higher yield may beobtained per unit of area. A further mechanism of yield increase usinggrowth inhibitors resides in the fact that nutrients are ableincreasingly to promote flower formation and fruiting, whereasvegetative growth is inhibited.

At higher rates of application of compounds of formula I, all testedplants are so severely damaged in their development that they die.

The invention also relates to herbicidal and plant growth regulatingcompositions which contain a novel a compound of formula I, and also tomethods of controllibng weeds pre- and postemergence and of inhibitingthe growth of monocots and dicots, especially grasses, tropical covercrops and tobacco plant suckers.

The compounds of formula I are used in unmodified form or, preferablytogether with the adjuvants conventionally employed in the art offormulation, and are therefore formulated in known manner toemulsifiable concentrates, directly sprayable or dilutable solutions,dilute emulsions, wettable powders, soluble powders, dusts, granulates,and also encapsulation in e.g. polymer substances. As with the nature ofthe compositions, the methods of application, such as spraying,atomising, dusting, scattering or pouring, are chosen in accordance withthe intended objectives and the prevailing circumstances.

The formulations, i.e. the compositions, preparations or mixturescontaining the compound (active ingredient) of formula I and, whereappropriate, a solid or liquid adjuvant, are prepared in known manner,e.g. by homogeneously mixing and/or grinding the active ingredients withextenders, e.g. solvents, solid carriers and, where appropriate,surface-active compounds (surfactants).

Suitable solvents are: aromatic hydrocarbons, preferably the fractionscontaining 8 to 12 carbon atoms, e.g. xylene mixtures or substitutednaphthalene, phthalates such as dibutyl phthalate or dioctyl phthalate,aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols andglycols and their ethers and esters, such as ethanol, ethylene glycol,ethylene glycol monomethyl or monoethyl ether, ketones such ascyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone,dimethyl sulfoxide or dimethylformamide, as well as vegetable oils orepoxidised vegetable oils such as epoxidised coconut oil or soybean oil;or water.

The solid carriers used e.g. for dusts and dispersible powders arenormally natural mineral fillers such as calcite, talcum, kaolin,montmorillonite or attapulgite. In order to improve the physicalproperties is is also possible to add highly dispersed silicic acid orhighly dispersed absorbent polymers. Suitable granulted adsorptivecarriers are porous types, for example pumice, broken brick, sepioliteor bentonite; and suitable nonsorbent carriers are materials such ascalcite or sand. In addition, a great number of pregranulated materialsof inorganic or organic nature can be used, e.g. especially dolomite orpulverised plant residues.

Depending on the nature of the compound of formula I to be formulated,suitable surface-active compounds are non-ionic, cationic and/or anionicsurfactants having good emulsifying, dispersing and wetting properties.The term "surfactants" will also be understood as comprising mixtures ofsurfactants.

Suitable anionic surfactants can be both water-soluble soaps andwater-soluble synthetic surface-active compounds.

Suitable sopas are the alkali metal salts, alkaline earth metal salts orunsubstituted or substituted ammonium salts of higher fatty acids (C₁₀-C₂₂), e.g. the sodium or potassium salts of oleic or stearic acid, orof natural fatty acid mixtures which can be obtained e.g. from coconutoil or tallow oil. Mention may also be made of fatty acid methyltaurinsalts.

More frequently, however, so-called synthetic surfactants are used,especially fatty sulfonates, fatty sulfates, sulfonated benzimidazolederivatives or alkylarylsulfonates.

The fatty sulfonates or sulfates are usually in the form of alkali metalsalts, alkaline earth metal salts or unsubstituted or substitutedammonium salts and contain a C₈ -C₂₂ alkyl radical which also includesthe alkyl moiety of acyl radicals, e.g. the sodium or calcium salt oflignosulfonic acid, of dodecylsulfate or of a mixture of fatty alcoholsulfates obtained from natural fatty acids. These compounds alsocomprise the salts of sulfuric acid esters and sulfonic acids of fattyalcohol/ethylene oxide adducts. The sulfonated benzimidazole derivativespreferably contain 2 sulfonic acid groups and one fatty acid radicalcontaining 8 to 22 carbon atoms. Examples of alkylarylsulfonates are thesodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid,dibutylnaphthalenesulfonic acid, or of a naphthalenesulfonicacid/formaldehyde condensation product.

Also suitable are corresponding phosphates, e.g. salts of the phosphoricacid ester of an adduct of p-nonylphenol with 4 to 14 moles of ethyleneoxide, or phospholipids.

Non-ionic surfactants are preferably polyglycol ether derivatives ofaliphatic or cycloaliphatic alcohols, or saturated and unsaturated fattyacids and alkylphenols, said derivatives containing 3 to 10 glycol ethergroups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moietyand 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.

Further suitable non-ionic surfactants are the water-soluble adducts ofpolyethylene oxide with polypropylene glycol,ethylenediaminopolypropylene glycol and alkylpolypropylene glycolcontaining 1 to 10 carbon atoms in the alkyl chain, which adductscontain 20 to 250 ethylene glycol ether groups and 10 to 100 propyleneglycol ether groups. These compounds usually contain 1 to 5 ethyleneglycol units per propylene glycol unit.

Representative examples of non-ionic surfactants arenonylphenolpolyethoxyethanols, castor oil polyglycol ethers,polypropylene/polyethylene oxide adducts,tributylphenoxypolyethoxyethanol, polyethylene glycol andoctylphenoxypolyethoxyethanol.

Fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylenesorbitan trioleate, are also suitable non-ionic surfactants.

Cationic surfactants are preferably quaternary ammonium salts whichcontain, as N-substituent, at least one C₈ -C₂₂ alkyl radical and, asfurther substituents, unsubstituted or halogenated lower alkyl, benzylor hydroxy-lower alkyl radicals. The salts are preferably in the form ofhalides, methylsulfates or ethylsulfates, e.g. stearyltrimethylammoniumchloride or benzyldi(2-chloroethyl)ethylammonium bromide.

The surfactants customarily employed in the art of formulation aredescribed e.g. in the following publications: "McCutcheon's Detergentsand Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., 1981; H.Stache, "Tensid-Taschenbuch" (Handbood of Surfactants), C. HanserVerlag, Munich & Vienna, 1981.

The ready-for-use preparations usually contain 0.1 to 95%, preferably0.1 to 80%, of a compound of formula I, 1 to 99.9% of a solid or liquidadjuvant, and 0 to 25%, preferably 0.1 to 25%, of a surfactant.

Preferred formulations are composed in particular of the followingconstituents (%=percentage by weight):

Emulsifiable concentrates

compound of formula I: 1 to 20%, preferably 5 to 10%

surfactant: 5 to 30%, preferably 10 to 20%

liquid carrier: 50 to 94%, preferably 70 to 85%

Dusts

compound of formula I: 0.1 to 10%, preferably 0.1 to 1%

solid carrier: 99.9 to 90%, preferably 99.9 to 99%

Suspension concentrates

compound of formula I: 5 to 75%, preferably 10 to 50%

water: 94 to 25%, preferably 90 to 30%

surfactant: 1 to 40%, preferably 2 to 30%

Wettable powders

compound of formula I: 0.5 to 90%, preferably 1 to 80%

surfactant: 0.5 to 20%, preferably 1 to 15%

solid carrier: 5 to 95%, preferably 15 to 90%

Granulates

compound of formula I: 0.5 to 30%, preferably 3 to 15%

solid carrier: 99.5 to 70%, preferably 97 to 85%.

Whereas commercial products will be preferably formulated asconcentrates, the end user will normally employ dilute formulations. Theformulations can be diluted to a concentration as low as 0.001% ofactive ingredient. The rates of application are usually from 0.005 to 5kg a.i./ha.

The compositions may also contain further ingredients such asstabilisers, antifoams, viscosity regulators, binders, tackifiers, aswell as fertilisers and other compounds of obtaining special effects.

The following Example illustrates the preparation of a compound offormula I. Further compounds prepared in corresponding manner are listedin the subsequent Table.

EXAMPLE 1 Preparation of 4-pyridylmethyl2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-5-methylnicotinate##STR8##

7.71 g (=0.03 mole) of3,5-dioxo-2-isopropyl-2,8-dimethyl-2,3-dihydroimidazo[1',2':1,2]-5H-pyrrolo[3,4-b]pyridine,3.27 g of 4-hydroxymethylpyridine and 4 drops of1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are heated under refluxovernight in 150 ml of toluene. The solvent is then evaporated off andthe residue is crystallised from a mixture of methylene chloride andhexane. Yield: 9.5 g (=87% of theory). Melting point: 182°-184° C.

The3,5-dioxo-2-isopropyl-2,8-dimethyl-2,3-dihydroimidazo[1',2':1,2]-5-H-pyrrole[3,4-b]pyridinerequired as starting material is prepared as follows: ##STR9## Withstirring, 13.1 g (0.05 mole) of2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)nicotinic acidare added to a solution of 11.1 g of dicyclohexylcarbodiimide (DCC) in100 ml of methylene chloride. Stirring is continued for a further 2hours at room temperature. The resultant dicyclohexylurea is removed bysuction filtration and the residue is washed with a small amount ofmethylene chloride. The filtrate is concentrated by evaporation and theresidue is recrystallised from a mixture of ethyl acetate and hexane,affording the title product in 86% yield (10.4 g) in the form ofcrystals which melt at 132°-133° C.

The following starting materials are obtained in analogous manner:

    ______________________________________                                         ##STR10##                                                                    X              X     Physical data                                            ______________________________________                                        nC.sub.3 H.sub.7                                                                             H     m.p. 132-133° C.                                  CH(CH.sub.3).sub.2                                                                           H     m.p. 145-146° C.                                  C.sub.2 H.sub.5                                                                              H     m.p. 136-138° C.                                  n-C.sub.4 H.sub.9                                                                            H     m.p. 116-119° C.                                  CH.sub.3       H     m.p. 129-131° C.                                  ______________________________________                                    

The following compounds are obtained in the same manner by using thecorresponding starting materials:

                                      TABLE 1                                     __________________________________________________________________________     ##STR11##                                                                    Comp.                                                                             X      Y     A      Het           m.p.                                    __________________________________________________________________________    1.001                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             pyridin-4-yl  182-184° C.                                                            Example 1                               1.002                                                                             CH.sub.3                                                                             H     CH.sub.2 CH.sub.2                                                                    indol-2-yl    146-149° C.                      1.003                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2 CH.sub.2                                                                    indol-2-yl    166-168° C.                      1.004                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2 CH.sub.2                                                                    pyridin-2-yl  resin                                   1.005                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2 CH.sub.2                                                                    isoindol-1,3-dion-2-yl                                                                      130-131° C.                      1.006                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             pyridin-2-yl  80-82° C.                        1.007                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             pyridin-3-yl  123-124° C.                      1.008                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             pyridin-4-yl  135- 137° C.                     1.009                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             pyridin-3-yl  133-134° C.                      1.010                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             pyridin-2-yl  172-173° C.                      1.011                                                                             H      H     CH.sub.2 CH.sub.2                                                                    pyridin-2-yl  105-106° C.                      1.012                                                                             CH.sub.3                                                                             H     CH.sub.2 CH.sub.2                                                                    pyridin-2-yl  119-122° C.                      1.013                                                                             H      H     CH(CH.sub.3)                                                                         pyridin-4-yl                                          1.014                                                                             (CHCH).sub.2 CH.sub.2 CH.sub.2                                                                    pyridin-4-yl                                          1.015                                                                             (CHCH).sub.2 CH.sub.2                                                                             pyridin-4-yl                                          1.016                                                                             (CHCH).sub.2 CH.sub.2                                                                             pyridazin-2-yl                                        1.017                                                                             (CHCH).sub.2 CH.sub.2                                                                             pyrrol-l-yl                                           1.018                                                                             H      H     CH.sub.2 CH.sub.2                                                                    pyrrol-1-yl                                           1.019                                                                             H      H     CH.sub.2                                                                             pyrrol-1-yl                                           1.020                                                                             H      H     CH.sub.2 CH.sub.2                                                                    imidazol-1-yl                                         1.021                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             imidazol-1-yl                                         1.022                                                                             H      H     CH.sub.2                                                                             1H1,2,4-triazol-1-yl                                  1.023                                                                             CH.sub.3                                                                             H     CH.sub.2 CH.sub.2                                                                    1H1,2,4-triazol-1-yl                                  1.024                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             1H1,3,4-triazol-1-yl                                  1.025                                                                             H      H     CH.sub.2 CH.sub.2                                                                    1H1,3,4-triazol-1-yl                                  1.026                                                                             H      H     CH.sub.2                                                                             pyrimidin-4-yl                                        1.027                                                                             CH.sub.3                                                                             H     CH(CH.sub.3)CH.sub.2                                                                 pyrimidin-4-yl                                        1.028                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             pyrimidin-2-yl                                        1.029                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             pyrimidin-2-yl                                        1.030                                                                             H      H     CH.sub.2 CH.sub.2                                                                    indol-3-yl                                            1.031                                                                             CH.sub. 3                                                                            H     CH.sub.2                                                                             indol-3-yl                                            1.032                                                                             (CHCH).sub.2 CH.sub.2                                                                             4-methylpyridin-2-yl                                  1.033                                                                             (CHCH).sub.2 CH.sub.2                                                                             pyrimidin-2-yl                                        1.034                                                                             (CHCH).sub.2 CH.sub.2                                                                             indol-2-yl                                            1.035                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             tetrahydrofur-2-yl                                                                          113-115° C.                      1.036                                                                             CH.sub.3                                                                             H     CH.sub.2 CH.sub.2                                                                    indol-2-yl    146-149° C.                      1.037                                                                             H      H     C.sub.3 H.sub.6                                                                      pyrazol-4-yl  168-172° C.                      1.038                                                                             CH.sub.3                                                                             H     CH.sub.2 CH.sub.2                                                                    phthalimido   151-153° C.                      1.039                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             furfurol-5-yl resin                                   1.040                                                                             H      H     C.sub.3 H.sub.6                                                                      1,2-oxazol-4-yl                                                                             oil                                     1.041                                                                             H      H     CH.sub.2                                                                             pyridin-2-yl  111-112° C.                      1.042                                                                             H      H     CH.sub.2                                                                             pyridin-3-yl  137-138° C.                      1.043                                                                             H      H     CH.sub.2                                                                             pyridin-4-yl  155-157° C.                      1.044                                                                             H      H     CH.sub.2 CH.sub.2                                                                    indol-2-yl    resin                                   1.045                                                                             H      H     CH.sub.2 CH.sub.2                                                                    phthalimido   resin                                   1.046                                                                             H      H     CH.sub.2                                                                             tetrahydrofur-2-yl                                    1.047                                                                             H      H     C.sub.3 H.sub.6                                                                      1-phenylpyrazol-4-yl                                                                        118-119° C.                      1.048                                                                             H      H     C.sub.3 H.sub.6                                                                      1-methylpyrazol-4-yl                                                                        134-135° C.                      1.049                                                                             H      H     C.sub.3 H.sub.6                                                                      1-ethylpyrazol-4-yl                                                                         87-88° C.                        1.050                                                                             C.sub.2 H.sub. 5                                                                     H     C.sub.3 H.sub.6                                                                      1-methylpyrazol-4-yl                                                                        90-92° C.                        1.051                                                                             C.sub.2 H.sub.5                                                                      H     C.sub.3 H.sub.6                                                                      1,2-oxazl-4-yl                                                                              90-92° C.                        1.052                                                                             C.sub.2 H.sub.5                                                                      H     C.sub.3 H.sub.6                                                                      1-ethylpyrazol-4-yl                                                                         resin                                   1.053                                                                             (CHCH).sub.2 CH.sub.2                                                                             1-ethylpyrazol-4-yl                                                                         resin                                   1.054                                                                             C.sub.3 H.sub.7 n                                                                    H     CH.sub.2                                                                             pyridin-4-yl  110° C.                          1.055                                                                             C.sub.3 H.sub.7 n                                                                    H     C.sub.2 H.sub.4                                                                      pyridin-2-yl  108° C.                          1.056                                                                             C.sub.3 H.sub.7 n                                                                    H     CH.sub.2                                                                             tetrahydrofur-2-yl                                                                          87-90° C.                        1.057                                                                             H      H     CH.sub.2 CH.sub.2                                                                    1,2-oxazol-4-yl                                                                             resin                                   1.058                                                                             CH.sub.3                                                                             H     CH.sub.2 CH.sub.2                                                                    1,2-oxazol-4-yl                                                                             oil                                     1.059                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2 CH.sub.2                                                                    1,2-oxazol-4-yl                                                                             oil                                     1.060                                                                             (CHCH).sub.2 CH.sub.2 CH.sub.2                                                                    1.2-oxazol-4-yl                                       1.061                                                                             Cl     H     CH.sub.2 CH.sub.2                                                                    1,2-oxazol-4-yl                                       1.062                                                                             CHCClCHCH    CH.sub.2 CH.sub.2                                                                    1,2-oxazol-4-yl                                       1.063                                                                             Br     H     CH.sub.2 CH.sub.2                                                                    1,2-oxazol-4-yl                                       1.064      CH(CH.sub.3).sub.2                                                                  CH.sub.2 CH.sub.2                                                                    1,2-oxazol-4-yl                                       1.065                                                                             H      H     CH.sub. 2 CH.sub.2                                                                   pyrazol-4-yl                                          1.066                                                                             H      H     CH.sub.2 CH.sub.2                                                                    1-methylpyrazol-4-yl                                  1.067                                                                             H      H     CH.sub.2 CH.sub.2                                                                    1-ethylpyrazol-4-yl                                   1.068                                                                             H      H     CH.sub.2 CH.sub.2                                                                    1-phenylpyrazol-4-yl                                                                        131-132° C.                      1.069                                                                             CH.sub.3                                                                             H     CH.sub.2 CH.sub.2                                                                    pyrazol-4-yl                                          1.070                                                                             CH.sub.3                                                                             H     CH.sub.2 CH.sub.2                                                                    1-methylpyrazol-4-yl                                  1.071                                                                             CH.sub.3                                                                             H     CH.sub.2 CH.sub.2                                                                    1-ethylpyrazol-4-yl                                   1.072                                                                             CH.sub.3                                                                             H     CH.sub.2 CH.sub.2                                                                    1-phenylpyrazol-4-yl                                  1.073                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2 CH.sub.2                                                                    pyrazol-1-yl  148-151° C.                      1.074                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2 CH.sub.2                                                                    1-methylpyrazol-4-yl                                  1.075                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2 CH.sub.2                                                                    1-ethylpyrazol-4-yl                                   1.076                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2 CH.sub.2                                                                    1-phenylpyrazol-4-yl                                                                        vitreous                                1.077                                                                             (CHCH).sub.2 CH.sub.2 CH.sub.2                                                                    pyrazol-4-yl                                          1.078                                                                             (CHCH).sub.2 CH.sub.2 CH.sub.2                                                                    1-methylpyrazol-4-yl                                  1.079                                                                             (CHCH).sub.2 CH.sub.2 CH.sub.2                                                                    1-ethylpyrazol-4-yl                                   1.080                                                                             (CHCH).sub.2 CH.sub.2 CH.sub.2                                                                    1-phenylpyrazol-4-yl                                                                        solid                                   1.081                                                                             Cl     H     CH.sub.2 CH.sub.2                                                                    pyrazol-4-yl                                          1.082                                                                             Cl     H     CH.sub.2 CH.sub.2                                                                    1-methylpyrazol-4-yl                                  1.083                                                                             Cl     H     CH.sub.2 CH.sub.2                                                                    1-ethylpyrazol-4-yl                                   1.084                                                                             Cl     H     CH.sub.2 CH.sub.2                                                                    1-phenylpyrazol-4-yl                                  1.085                                                                             CHCClCHCH    CH.sub.2 CH.sub.2                                                                    pyrazol-4-yl                                          1.086                                                                             CHCClCHCH    CH.sub.2 CH.sub.2                                                                    1-methylpyrazol-4-yl                                  1.087                                                                             CHCClCHCH    CH.sub.2 CH.sub.2                                                                    1-ethylpyrazol-4-yl                                   1.088                                                                             CHCClCHCH    CH.sub.2 CH.sub.2                                                                    1-phenylpyrazol-4-yl                                  1.089                                                                             Br     H     CH.sub.2 CH.sub.2                                                                    pyrazol-4-yl                                          1.090                                                                             Br     H     CH.sub.2 CH.sub.2                                                                    1-methylpyrazol-4-yl                                  1.091                                                                             Br     H     CH.sub.2 CH.sub.2                                                                    1-ethylpyrazol-4-yl                                   1.092                                                                             Br     H     CH.sub.2 CH.sub.2                                                                    1-phenylpyrazol-4-yl                                  1.093                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2 CH.sub.2                                                                    pyrazol-4-yl                                          1.094                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2 CH.sub.2                                                                    1-methylpyrazol-4-yl                                  1.095                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2 CH.sub.2                                                                    1-ethylpyrazol-4-yl                                   1.096                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2 CH.sub.2                                                                    1-phenylpyrazol-4-yl                                  1.097                                                                             H      H     CH.sub.2 CH.sub.2                                                                    3,5-dibromooxazol-4-yl                                1.098                                                                             CH.sub.3                                                                             H     CH.sub.2 CH.sub.2                                                                    3,5-dibromooxazol-4-yl                                1.099                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2 CH.sub.2                                                                    3,5-dibromooxazol-4-yl                                1.100                                                                             (CHCH).sub.2 CH.sub.2 CH.sub.2                                                                    3,5-dibromooxazol-4-yl                                1.101                                                                             Cl     H     CH.sub.2 CH.sub.2                                                                    3,5-dibromooxazol-4-yl                                1.102                                                                             CHCClCHCH    CH.sub.2 CH.sub.2                                                                    3,5-dibromooxazol-4-yl                                1.103                                                                             Br     H     CH.sub.2 CH.sub.2                                                                    3,5-dibromooxazol-4-yl                                1.104                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2 CH.sub.2                                                                    3,5-dibromooxazol-4-yl                                1.105                                                                             H      H     CH.sub.2                                                                             benzimidazol-2-yl                                     1.106                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             benzimidazol-2-yl                                     1.107                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             benzimidazol-2-yl                                     1.108                                                                             (CHCH).sub.2 CH.sub.2                                                                             benzimidazol-2-yl                                     1.109                                                                             Cl     H     CH.sub.2                                                                             benzimidazol-2-yl                                     1.110                                                                             CHCClCHCH    CH.sub.2                                                                             benzimidazol-2-yl                                     1.111                                                                             Br     H     CH.sub.2                                                                             benzimidazol-2-yl                                     1.112                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2                                                                             benzimidazol-2-yl                                     1.113                                                                             H      H     CH.sub.2                                                                             imidazol-2-yl                                         1.114                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             imidazol-2-yl                                         1.115                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             imidazol-2-yl                                         1.116                                                                             (CHCH).sub.2 CH.sub.2                                                                             imidazol-2-yl                                         1.117                                                                             Cl     H     CH.sub.2                                                                             imidazol-2-yl                                         1.118                                                                             CHCClCHCH    CH.sub.2                                                                             imidazol-2-yl                                         1.119                                                                             Br     H     CH.sub.2                                                                             imidazol-2-yl                                         1.120                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2                                                                             imidazol-2-yl                                         1.121                                                                             H      H     CH.sub.2                                                                             benzoxazol-2-yl                                       1.122                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             benzoxazol-2-yl                                       1.123                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             benzoxazol-2-yl                                       1.124                                                                             (CHCH).sub.2 CH.sub.2                                                                             benzoxazol-2-yl                                       1.125                                                                             Cl     H     CH.sub.2                                                                             benzoxazol-2-yl                                       1.126                                                                             CHCClCHCH    CH.sub.2                                                                             benzoxazol-2-yl                                       1.127                                                                             Br     H     CH.sub.2                                                                             benzoxazol-2-yl                                       1.128                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2                                                                             benzoxazol-2-yl                                       1.129                                                                             H      H     CH(CH.sub.3)CH.sub.2                                                                 3-hydroxy-1,2-oxazol-5-yl                             1.130                                                                             CH.sub.3                                                                             H     CH(CH.sub.3)CH.sub.2                                                                 3-hydroxy-1,2-oxazol-5-yl                             1.131                                                                             C.sub.2 H.sub.5                                                                      H     CH(CH.sub.3)CH.sub.2                                                                 3-hydroxy-1,2-oxazol-5-yl                             1.132                                                                             (CHCH).sub.2 CH(CH.sub.3)CH.sub.2                                                                 3-hydroxy-1,2-oxazol-5-yl                             1.133                                                                             Cl     H     CH(CH.sub.3)CH.sub.2                                                                 3-hydroxy-1,2-oxazol-5-yl                             1.134                                                                             CHCClCHCH    CH(CH.sub.3)CH.sub.2                                                                 3-hydroxy-1,2-oxazol-5-yl                             1.135                                                                             Br     H     CH(CH.sub.3)CH.sub.2                                                                 3-hydroxy-1,2-oxazol-5-yl                             1.136                                                                             H      CH(CH.sub.3).sub.2                                                                  CH(CH.sub.3)CH.sub.2                                                                 3-hydroxy-1,2-oxazol-5-yl                             1.137                                                                             H      H     (CH.sub.2).sub.4                                                                     2-methylpyridin-4-yl                                  1.138                                                                             CH.sub.3                                                                             H     (CH.sub.2).sub.4                                                                     2-methylpyridin-4-yl                                  1.139                                                                             C.sub.2 H.sub.5                                                                      H     (CH.sub.2).sub.4                                                                     2-methylpyridin-4-yl                                  1.140                                                                             (CHCH).sub.2 (CH.sub.2).sub.4                                                                     2-methylpyridin-4-yl                                  1.141                                                                             Cl     H     (CH.sub.2).sub.4                                                                     2-methylpyridin-4-yl                                  1.142                                                                             CHCClCHCH    (CH.sub.2 ).sub.4                                                                    2-methylpyridin-4-yl                                  1.143                                                                             Br     H     (CH.sub.2).sub.4                                                                     2-methylpyridin-4-yl                                  1.144                                                                             H      CH(CH.sub.3).sub.2                                                                  (CH.sub.2).sub.4                                                                     2-methylpyridin-4-yl                                  1.145                                                                             H      H     CH.sub.2                                                                             3-methyl-1,2,4-triazol-5-yl                           1.146                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             3-methyl-1,2,4-triazol-5-yl                           1.147                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             3-methyl-1,2,4-triazol-5-yl                           1.148                                                                             (CHCH).sub.2 CH.sub.3                                                                             3-methyl-1,2,4-triazol-5-yl                           1.149                                                                             Cl     H     CH.sub.2                                                                             3-methyl-1,2,4-triazol-5-yl                           1.150                                                                             CHCClCHCH    CH.sub.2                                                                             3-methyl-1,2,4-triazol-5-yl                           1.151                                                                             Br     H     CH.sub.2                                                                             3-methyl-1,2,4-triazol-5-yl                           1.152                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2                                                                             3-methyl-1,2,4-triazol-5-yl                           1.153                                                                             H      H     CH.sub.2                                                                             1,3,4-oxadiazol-2-yl                                  1.154                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             1,3,4-oxadiazol-2-yl                                  1.155                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             1,3,4-oxadiazol-2-yl                                  1.156                                                                             (CHCH).sub.2 CH.sub.2                                                                             1,3,4-oxadiazol-2-yl                                  1.157                                                                             Cl     H     CH.sub.2                                                                             1,3,4-oxadiazol-2-yl                                  1.158                                                                             CHCClCHCH    CH.sub.2                                                                             1,3,4-oxadiazol-2-yl                                  1.159                                                                             Br     H     CH.sub.2                                                                             1,3,4-oxadiazol-2-yl                                  1.160                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2                                                                             1,3,4-oxadiazol-2-yl                                  1.161                                                                             H      H     CH.sub.2                                                                             4-nitropyridin-2-yl                                   1.162                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             4-nitropyridin-2-yl                                   1.163                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub. 2                                                                            4-nitropyridin-2-yl                                   1.164                                                                             (CHCH).sub.2                                                                         H     CH.sub.2                                                                             4-nitropyridin-2-yl                                   1.165                                                                             Cl     H     CH.sub.2                                                                             4-nitropyridin-2-yl                                   1.166                                                                             CHCClCHCH    CH.sub.2                                                                             4-nitropyridin-2-yl                                   1.167                                                                             Br     H     CH.sub.2                                                                             4-nitropyridin-2-yl                                   1.168                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2                                                                             4-nitropyridin-2-yl                                   1.169                                                                             H      H     CH.sub.2                                                                             4-chloropyridin-2-yl                                  1.170                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             4-chloropyridin-2-yl                                  1.171                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             4-chloropyridin-2-yl                                  1.172                                                                             (CHCH).sub.2                                                                         H     CH.sub.2                                                                             4-chloropyridin-2-yl                                  1.173                                                                             Cl     H     CH.sub.2                                                                             4-chloropyridin-2-yl                                  1.174                                                                             CHCClCHCH    CH.sub.2                                                                             4-chloropyridin-2-yl                                  1.175                                                                             Br     H     CH.sub.2                                                                             4-chloropyridin-2-yl                                  1.176                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2                                                                             4-chloropyridin-2-yl                                  1.177                                                                             H      H     CH.sub.2                                                                             2-chloropyridin-6-yl                                  1.178                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             2-chloropyridin-6-yl                                  1.179                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             2-chloropyridin-6-yl                                  1.180                                                                             (CHCH).sub.2 CH.sub.2                                                                             2-chloropyridin-6-yl                                  1.181                                                                             Cl     H     CH.sub.2                                                                             2-chloropyridin-6-yl                                  1.182                                                                             CHCClCHCH    CH.sub.2                                                                             2-chloropyridin-6-yl                                  1.183                                                                             Br     H     CH.sub.2                                                                             2-chloropyridin-6-yl                                  1.184                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2                                                                             2-chloropyridin-6-yl                                  1.185                                                                             H      H     CH.sub.2                                                                             quinolin-2-yl                                         1.186                                                                             CH.sub. 3                                                                            H     CH.sub.2                                                                             quinolin-2-yl                                         1.187                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             quinolin-2-yl                                         1.188                                                                             (CHCH).sub.2 CH.sub.2                                                                             quinolin-2-yl                                         1.189                                                                             Cl     H     CH.sub.2                                                                             quinolin-2-yl                                         1.190                                                                             CHCClCHCH    CH.sub.2                                                                             quinolin-2-yl                                         1.191                                                                             Br     H     CH.sub.2                                                                             quinolin-2-yl                                         1.192                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2                                                                             quinolin-2-yl                                         1.193                                                                             H      H     CH.sub.2                                                                             4-nitroquinolin-2-yl                                  1.194                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             4-nitroquinolin-2-yl                                  1.195                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             4-nitroquinolin-2-yl                                  1.196                                                                             (CHCH).sub.2 CH.sub.2                                                                             4-nitroquinolin-2-yl                                  1.197                                                                             Cl     H     CH.sub.2                                                                             4-nitroquinolin-2-yl                                  1.198                                                                             CHCClCHCH    CH.sub.2                                                                             4-nitroquinolin-2-yl                                  1.199                                                                             Br     H     CH.sub.2                                                                             4-nitroquinolin-2-yl                                  1.200                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2                                                                             4-nitroquinolin-2-yl                                  1.201                                                                             H      H     CH.sub.2                                                                             quinoxalin-2-yl                                       1.202                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             quinoxalin-2-yl                                       1.203                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             quinoxalin-2-yl                                       1.204                                                                             (CHCH).sub.2 CH.sub.2                                                                             quinoxal-2-yl                                         1.205                                                                             Cl     H     CH.sub.2                                                                             quinoxal-2-yl                                         1.206                                                                             CHCClCHCH    CH.sub.2                                                                             quinoxal-2-yl                                         1.207                                                                             Br     H     CH.sub.2                                                                             quinoxal-2-yl                                         1.208                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2                                                                             quinoxal-2-yl                                         1.209                                                                             H      H     CH(CH.sub.3)CH.sub.2                                                                 4-chloropyridin-2-yl                                  1.210                                                                             CH.sub.3                                                                             H     CH(CH.sub.3)CH.sub.2                                                                 4-chloropyridin-2-yl                                  1.211                                                                             C.sub.2 H.sub.5                                                                      H     CH(CH.sub.3)CH.sub.2                                                                 4-chloropyridin-2-yl                                  1.212                                                                             (CHCH) H     CH(CH.sub.3)CH.sub.2                                                                 4-chloropyridin-2-yl                                  1.213                                                                             Cl     H     CH(CH.sub.3)CH.sub.2                                                                 4-chloropyridin-2-yl                                  1.214                                                                             CHCClCHCH    CH(CH.sub.3)CH.sub.2                                                                 4-chloropyridin-2-yl                                  1.215                                                                             Br     H     CH(CH.sub.3)CH.sub.2                                                                 4-chloropyridin-2-yl                                  1.216                                                                             H      CH(CH.sub.3).sub.2                                                                  CH(CH.sub.3)CH.sub.2                                                                 4-chloropyridin-2-yl                                  1.217                                                                             H      H     CH.sub.2                                                                             2,4-dichloropyridin-6-yl                              1.218                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             2,4-dichloropyridin-6-yl                              1.219                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             2,4-dichloropyridin-6-yl                              1.220                                                                             (CHCH).sub.2 CH.sub.2                                                                             2,4-dichloropyridin-6-yl                              1.221                                                                             Cl     H     CH.sub.2                                                                             2,4-dichloropyridin-6-yl                              1.222                                                                             CHCClCHCH    CH.sub.2                                                                             2,4-dichloropyridin-6-yl                              1.223                                                                             Br     H     CH.sub.2                                                                             2,4-dichloropyridin-6-yl                              1.224                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2                                                                             2,4-dichloropyridin-6-yl                              1.225                                                                             H      H     CH.sub.2                                                                             4-methoxypyrimidin-2-yl                               1.226                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             4-methoxypyrimidin-2-yl                               1.227                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             4-methoxypyrimidin-2-yl                               1.228                                                                             (CHCH).sub.2 CH.sub.2                                                                             4-methoxypyrimidin-2-yl                               1.229                                                                             Cl     H     CH.sub.2                                                                             4-methoxypyrimidin-2-yl                               1.230                                                                             CHCClCHCH    CH.sub.2                                                                             4-methoxypyrimidin-2-yl                               1.231                                                                             Br     H     CH.sub.2                                                                             4-methoxypyrimidin-2-yl                               1.232                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2                                                                             4-methoxypyrimidin-2-yl                               1.233                                                                             H      H     CH(CH.sub.3)CH.sub.2                                                                 pyridin-4-yl                                          1.234                                                                             CH.sub.3                                                                             H     CH(CH.sub.3)CH.sub.2                                                                 pyridin-4-yl                                          1.235                                                                             C.sub.2 H.sub.5                                                                      H     CH(CH.sub.3)CH.sub.2                                                                 pyridin-4-yl                                          1.236                                                                             (CHCH).sub.2 CH(CH.sub.3)CH.sub.2                                                                 pyridin-4-yl                                          1.237                                                                             Cl     H     CH(CH.sub.3)CH.sub.2                                                                 pyridin-4-yl                                          1.238                                                                             CHCClCHCH    CH(CH.sub.3)CH.sub.2                                                                 pyridin-4-yl                                          1.239                                                                             Br     H     CH(CH.sub.3)CH.sub.2                                                                 pyridin-4-yl                                          1.240                                                                             H      CH(CH.sub.3).sub.2                                                                  CH(CH.sub.3)CH.sub.2                                                                 pyridin-4-yl                                          1.241                                                                             H      H     CH.sub.2                                                                             4-methoxypyrimidin-2-yl                               1.242                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             4-methoxypyrimidin-2-yl                               1.243                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             4-methoxypyrimidin-2-yl                               1.244                                                                             (CHCH).sub.2 CH.sub.2                                                                             4-methoxypyrimidin-2-yl                               1.245                                                                             Cl     H     CH.sub.2                                                                             4-methoxypyrimidin-2-yl                               1.246                                                                             CHCClCHCH    CH.sub. 2                                                                            4-methoxypyrimidin-2-yl                               1.247                                                                             Br     H     CH.sub.2                                                                             4-methoxypyrimidin-2-yl                               1.248                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2                                                                             4-methoxypyrimidin-2-yl                               1.249                                                                             H      H     CH.sub.2                                                                             pyrimidin-2-yl                                        1.250                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             pyrimidin-2-yl                                        1.251                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             pyrimidin-2-yl                                        1.252                                                                             (CHCH).sub.2 CH.sub.2                                                                             pyrimidin-2-yl                                        1,253                                                                             Cl     H     CH.sub.2                                                                             pyrimidin-2-yl                                        1.254                                                                             CHCClCHCH    CH.sub.2                                                                             pyrimidin-2-yl                                        1.255                                                                             Br     H     CH.sub.2                                                                             pyrimidin-2-yl                                        1.256                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2                                                                             pyrimidin-2-yl                                        1.257                                                                             H      H     CH(CH.sub.3)                                                                         pyridin-4-yl                                          1.258                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             pyridin-4-yl                                          1.259                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             pyridin-4-yl                                          1.260                                                                             (CHCH).sub.2 CH.sub.2                                                                             pyridin-4-yl                                          1.261                                                                             Cl     H     CH.sub.2                                                                             pyridin-4-yl                                          1.262                                                                             CHCClCHCH    CH.sub.2                                                                             pyridin-4-yl                                          1.263                                                                             Br     H     CH.sub.2                                                                             pyridin-4-yl                                          1.264                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2                                                                             pyridin-4-yl                                          1.265                                                                             H      H     CH.sub.2                                                                             1,3,4-triazin-5-on-2-yl                               1.266                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             1,3,4-triazin-5-on-2-yl                               1.267                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             1,3,4-triazin-5-on-2-yl                               1.268                                                                             (CHCH).sub.2 CH.sub.2                                                                             1,3,4-triazin-5-on-2-yl                               1.269                                                                             Cl     H     CH.sub.2                                                                             1,3,4-triazin-5-on-2-yl                               1.270                                                                             CHCClCHCH.sub.2                                                                            CH.sub.2                                                                             1,3,4-triazin-5-on-2-yl                               1.271                                                                             Br     H     CH.sub.2                                                                             1,3,4-triazin-5-on-2-yl                               1.272                                                                             H      CH(CH.sub.3).sub.2                                                                  CH.sub.2                                                                             1,3,4-triazin-5-on-2-yl                               1.273                                                                             C.sub.2 H.sub.5                                                                      H     (CH.sub.2).sub.3                                                                     1-phenylpyrazol-4-yl                                                                        143-147° C.                      1.274                                                                             (CHCH).sub.2 (CH.sub.2).sub.3                                                                     1Hpyrazol-4-yl                                                                              solid                                   1.275                                                                             (CHCH).sub.2 (CH.sub.2).sub.3                                                                     1-methylpyrazol-4-yl                                                                        117-118° C.                      1.276                                                                             (CHCH).sub.2 (CH.sub.2).sub.3                                                                     1-phenylpyrazol-4-yl                                                                        128-131° C.                      1.277                                                                             CH.sub.3                                                                             H     CH.sub.2                                                                             tetrahydropyran-2-yl                                                                        106-109° C.                      1.278                                                                             CH.sub.3                                                                             H     CH.sub.2 CH.sub.2                                                                    pyrazol-1-yl  102-104° C.                      1.279                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2 CH.sub.2                                                                    pyrimidin-5-yl                                                                              120-122° C.                      1.280                                                                             C.sub.2 H.sub.5                                                                      H     CH.sub.2                                                                             5-(4,5-dihydro-3-methyl-                                                                    oil                                                             thio-6-tert-butyl-1,3-                                                        triazin-5-on-2-yl-hydrazine                                                   oxime)furfur-2-yl                                     __________________________________________________________________________

FORMULATION EXAMPLES EXAMPLE 2 Formulation Examples for compounds offormula I (percentages are by weight)

    ______________________________________                                        (a) Wettable powders                                                                              (a)     (b)     (c)                                       ______________________________________                                        compound of Table 1 20%     60%     0.5%                                      sodium lignosulfonate                                                                             5%      5%      5%                                        sodium laurylsulfate                                                                              3%      --      --                                        sodium diisobutylnaphthalenesulfonate                                                             --      6%      6%                                        octylphenol polyethylene glycol ether                                                             --      2%      2%                                        (7-8 moles of ethylene oxide)                                                 highly dispersed silicic acid                                                                     5%      27%     27%                                       kaolin              67%     --      --                                        sodium chloride     --      --      59.5%                                     ______________________________________                                    

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording wettablepowders which can be diluted with water to give suspensions of thedesired concentration.

    ______________________________________                                        (b) Emulsifiable concentrates                                                                        (a)     (b)                                            ______________________________________                                        compound of Table 1    10%     1%                                             octylphenol polyethylene glycol ether                                                                3%      3%                                             (4-5 moles of ethylene oxide)                                                 calcium dodecylbenzenesulfonate                                                                      3%      3%                                             castor oil polyglycol ether                                                                          4%      4%                                             (36 moles of ethylene oxide)                                                  cyclohexanone          30%     10%                                            xylene mixture         50%     79%                                            ______________________________________                                    

Emulsions of any required concentration can be obtained from thisconcentrate by dilution with water.

    ______________________________________                                        (c) Dusts           (a)     (b)                                               ______________________________________                                        compound of Table 1  0.1%    1%                                               talcum              99.9%   --                                                kaolin              --      99%                                               ______________________________________                                    

Dusts which are ready for use are obtained by mixing the activeingredient with the carrier, and grinding the mixture in a suitablemill.

    ______________________________________                                        (d) Extruder granulates                                                                           (a)    (b)                                                ______________________________________                                        compound of Table 1 10%    1%                                                 sodium lignosulfonate                                                                              2%    2%                                                 carboxymethylcellulose                                                                             1%    1%                                                 kaolin              87%    96%                                                ______________________________________                                    

The active ingredient is mixed and ground with the adjuvants, and themixture is subsequently moistened with water. The mixture is extrudedand then dried in a steam of air.

    ______________________________________                                        (e) Coated granulate                                                          ______________________________________                                        compound of Table 1   3%                                                      polyethylene glycol (mol. wt. 200)                                                                  2%                                                      kaolin                94%                                                     ______________________________________                                    

The finely ground active ingredient is uniformly applied, in a mixer, tothe kaolin moistened with polyethylene glycol. Non-dusty coatedgranulates are obtained in this manner.

    ______________________________________                                        (f) Suspension concentrates                                                                           (a)    (b)                                            ______________________________________                                        compound of Table 1     40%    5%                                             ethylene glycol         10%    10%                                            nonylphenol polyethylene glycol ether                                                                  6%    1%                                             (15 moles of ethylene oxide)                                                  sodium lignosulfonate   10%    5%                                             carboxymethylcellulose   1%    1%                                             37% aqueous formaldehyde solution                                                                     0.2%     0.2%                                         silicone oil in the form of a 75%                                                                     0.8%     0.8%                                         aqueous emulsion                                                              water                   32%    77%                                            ______________________________________                                    

The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspensions of anydesired concentration can be obtained by dilution with water.

    ______________________________________                                        (g) Salt solution                                                             ______________________________________                                        compound of Table 1    5%                                                     isopropylamine         1%                                                     octylphenol polyethylene glycol ether                                                                3%                                                     (78 moles of ethylene oxide)                                                  water                  91%                                                    ______________________________________                                    

BIOLOGICAL EXAMPLES EXAMPLE 3 Preemergence herbicidal action

In a greenhouse, immediately after sowing the test plants in seeddishes, the surface of the soil is treated with an aqueous dispersion ofthe test compounds, obtained from a 25% emulsifiable concentrate.Concentrations of 4 kg of test compound per hectare are applied. Theseed dishes are kept in the greenhouse at 22°-25° C. and 50-70% relativehumidity. The test is evaluated 3 weeks later in accordance with thefollowing rating:

1 plant has not germinated or it has died

2-3 very severe damage

4 severe damage

5 moderate damage, stunted growth

6 damage, the plant can regenerate

7-8 slight damage

9 normal growth, as untreated plants

In this test, the compounds of Table 1 exhibit strong herbicidalactivity.

EXAMPLE 4 Postemergence herbicidal action (contact herbicide)

A number of weeds, both mono- and dicotyledonous, are sprayedpostemergence in the 4- to 6-leaf stage with an aqueous activeingredient dispersion at a rate of 4 kg of test compound per hectare andkept at 24°-26° C. and 45-60% relative humidity. The test is evaluated15 days later in accordance with the same rating as employed above. Inthis test, the compounds of Table 1 also exhibit strong to very strongherbicidal activity.

EXAMPLE 5 Preemergence herbicidal action

Plastic pots are filled with expanded vermiculite (density: 0.135 g/cm³; water-absorbing capacity: 0.565 l/l). After the non-adsorptivevermiculite has been saturated with an aqueous emulsion in deionisedwater which contains the test compound in a concentration of 70.8 ppm,seeds of the following plants are sown on the surface: Nasturtiumofficinalis, Agrostis tenuis, Stellaria media and Digitaria sanguinalis.The pots are then kept in a climatic chamber at 20° C., an illuminationof about 20 klux and a relative humidity of 70%. During the germinatingphase of 4 to 6 days, the pots are covered with lightpermeable materialand watered with deionised water to increase the local humidity. Afterthe 5th day, 0,5% of a commercial liquid fertiliser (Greenzit®) is addedto the water. The test is evaluated 12 days after sowing and the actionon the plants is assessed in accordance with the rating indicated inExample 3.

The results are given in Table 2:

                  TABLE 2                                                         ______________________________________                                              Rate of                                                                       appli-                                                                  Comp. cation   Nasturtium                                                                              Agrostis                                                                             Stellaria                                                                             Digitaria                             No.   ppm      officinalis                                                                             tenuis media   sang.                                 ______________________________________                                        1.001 100      2         2      2       2                                           10       2         2      2       2                                           1        2         2      2       2                                           0.1      3         3      3       3                                           0.01     3         3      3       3                                     1.009 100      2         2      2       2                                           10       2         2      2       2                                           1        2         2      2       2                                           0.1      3         3      3       3                                           0.01     5         5      5       5                                     1.010 100      2         2      2       2                                           10       2         2      2       2                                           1        2         2      2       2                                           0.1      3         3      3       4                                           0.01     4         4      4       4                                     1.011 100      2         2      2       2                                           10       2         2      2       2                                           1        3         3      3       3                                           0.1      4         4      3       3                                           0.01     4         4      4       4                                     1.012 100      2         2      2       2                                           10       2         2      2       2                                           1        3         3      3       3                                           0.1      4         4      4       4                                           0.01     5         5      4       4                                     A     100      2         2      1       2                                           10       2         2      2       2                                           1        4         6      2       3                                           0.1      9         9      7       7                                           0.01     9         9      9       9                                     ______________________________________                                    

A is ethyl2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazole-2-yl)-5-methylnicotinateknown from published European patent application No. 41 623.

EXAMPLE 6 Herbicidal action in wild rice (paddy rice)

The weeds Echinocloa crus galli and Monocharia vag., which occur inwater, are sown in plastic beakers (surface: 60 cm² ; volume: 500 ml).After sowing, the beakers are filled with water up to the surface of thesoil. 3 days after sowing, the water level is increased to slightlyabove the soil surface (3-5 mm). Application is effected 3 days aftersowing by spraying the beakers with an aqueous emulsion of the testcompounds. The rate of application corresponds to a concentration of 4kg of active ingredient per hectare (concentration of the spraymixture=550 l/ha). The beakers are then kept in the greenhouse underoptimum growth conditions for rice weeds, i.e. at 25°-30° C. and at highhumidity. The evaluation of the tests takes place 3 weeks afterapplication.

Evaluation is made in accordance with the linear rating indicated inExample 3.

The test compounds of Table 1 exhibited good activity in this test.

EXAMPLE 7 Growth inhibition of tropical leguminous cover crops

The test plants (Centrosema plumieri and Centrosema pubescens) arereared until fully grown and then cut back to a height of 60 cm. Theplants are sprayed 7 days layer with an aqueous emulsion of the testcompound. The test plants are kept at 70% relative humidity and 6000 luxartificial light for 14 hours per day, at day temperatures of 27° C. andnight temperatures of 21° C. The test is evaluated 4 weeks afterapplication by assessing and weighing the new growth compared withcontrols and by determining the phytotoxicity.

In this test, a marked reduction in new growth of the plants treatedwith compounds of Table 1 at concentrations of 500 to 3000 g/ha isobserved (less than 20% of the new growth of untreated control plants),without damage being caused to the test plants.

EXAMPLE 8 Growth regulation of soybeans

Soybeans of the "Hark" variety are sown in plastic containers in anearth/peat/sand mixture (6:3:1). The containers are put into a climaticchamber and the plants develop to the 5-6 trefoil leaf stage after about5 weeks by optimum control of temperature, light, fertiliser addition,and watering. The plants are then sprayed with an aqueous mixture of acompound of formula I until thoroughly wetted. The concentrationcorresponds to up to 100 g a.i. per hectare. Evaluation is made about 5weeks after application. Compared with untreated controls, the compoundsof Table 1 of the invention markedly increase the number and weight ofthe harvested siliquae on the leading shoot.

EXAMPLE 9 Growth inhibition of cereals

Summer barley (Hordeum vulgare) and summer rye (Secale) are sown insterilised soil in plastic beakers in a greenhouse and watered asrequired. The cereal shoots are treated about 21 days after sowing withan aqueous spray mixture of a compound of Table 1. The concentrationcorresponds to up to 100 g of active ingredient per hectare. Evaluationof the growth of the cereals is made 21 days after application. Acomparison with untreated controls shows that the new growth of treatedcereal plants is reduced (60-90% of the controls) and that the diameterof the stalks has in some cases increased.

EXAMPLE 10 Growth inhibition of grasses

Seeds of the grasses Lolium perenne, Poa pratensis, Festuca ovina,Dactylis glomerate and Cynodon dactylon ae sown in plastic dishes filledwith an earth/peat/sand mixture (6:3:1), in a greenhouse, and watered asrequired. The emergent grasses are cut back weekly to a height of 4 cm,and about 50 days after sowing and 1 day after the last cut are sprayedwith an aqueous spray mixture of a compound of Table 1. Theconcentration of test compound corresponds to a rate of application ofup to 500 g a.i. per hectare. The growth of the grasses is evaluated 21days after application. The test compounds of formula I effect areduction in new growth in the range of 10-30% in comparison withuntreated controls.

EXAMPLE 11 Desiccation and defoliation action

Cotton plants of the Deltapine variety are reared in earthen-ware potsin a greenhouse. After the capsules have formed, the plants are sprayedwith an aqueous formulation of compound No. 1 at rates of applicationcorresponding to 1.2, 0.6 and 0.3 kg/ha in field application. Untreatedplants act as controls. Evaluation of the test is made 3, 7 and 14 daysafter application of the active ingredient by determining the degree ofdefoliation (percentage of fallen leaves) and of desiccation (drying outof the leaves remaining on the plant).

In this test, plants treated with test compounds of Table 1 at rates ofapplication of 0.6 and 1.2 kg/ha are left after 7 days with only a fewdried out leaves (<80% defoliation and dessication).

What is claimed is:
 1. A heterocyclylalkyl ester of a2-imidazolinonenicotinic acid of formula I ##STR12## wherein A is astraight chain or branched C₁ -C₄ alkylene bridge,X and Y are eachindependently of the other hydrogen, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, C₁-C₃ alkoxy, C₁ -C₃ haloalkoxy or halogen, or X and Y together form thebutadiene bridge CH═CH--CH═CH, which may be substituted by halogen,cyano or C₁ -C₄ alkyl, and Het is a 5-membered heterocycle whichcontains two nitrogen atoms and which may further contain one or twocarbonyl groups, which heterocycle may also be substituted by halogen,C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkoxy,phenyl, nitro, amino, C₁ -C₃ alkylamino or di(C₁ -C₃)alkylamino.
 2. Aheterocyclylalkyl ester according to claim 1, whereinA is a methylene orethylene bridge which is unsubstituted or substituted by methyl, X ishydrogen or C₁ -C₃ alkyl, Y is hydrogen and Het is as defined inclaim
 1. 3. A heterocyclylalkyl ester according to claim 1, whereinA isthe methylene, ethyl-1-ene or ethyl-2-ene bridge, X is hydrogen or C₁-C₃ alkyl, Y is hydrogen and Het is an unsaturated 5-memberedheterocycle which contains two nitrogen atoms and which may furthercontain one or two carbonyl groups, which heterocycle may also besubstituted by methyl.
 4. A compound according to claim 1, whereinA is astraight chain C₁ -C₃ alkylene bridge, X and Y are each independently ofthe other hydrogen, halogen or C₁ -C₃ alkyl, or X and Y together formthe butadiene bridge CH═CH--CH═CH, which may be substituted by halogenand Het is a imidazole or pyrazole ring which may be substituted bymethyl, ethyl or phenyl.
 5. A compound according to claim 4, whereinX ishydrogen, chlorine, bromine, methyl or ethyl, Y is hydrogen orisopropyl, or X and Y together form the butadiene bridge CH═CH--CH═CHwhich may be monosubstituted by chlorine, and Het is an imidazol-1-yl,imidazol-2-yl, pyrazol-1-yl or a pyrazol-4-yl ring which pyrazol-4-ylring may be substituted in position 1 by methyl, ethyl or phenyl.
 6. Acompound according to claim 4, selected frompyrazol-4-yl-propyl2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-nicotinate,1-methyl-pyrazol-4-yl-propyl2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-nicotinate,1-ethyl-pyrazol-4-yl propyl2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-nicotinate,1-methyl-pyrazol-4-yl-propyl2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-5-ethyl-nicotinate,1-ethyl-pyrazol-4-yl-propyl2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-5-ethyl-nicotinate,3-(1-ethylpyrazol-4-yl-methoxycarbonyl)-2-(5-isopropyl-5-methyl-oxo--4,5-dihydroimidazolin-2-yl)-quinoline,1-phenyl-pyrazol-4-yl-ethyl2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-nicotinate,pyrazol-1-yl-ethyl2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-nicotinate,1-phenylpyrazol-4-yl-ethyl2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-5-ethyl-nicotinate,3-(1-phenylpyrazol-4-yl-ethoxycarbonyl)-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-quinoline,3-(pyrazol-4-yl-propyloxycarbonyl)-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-quinoline,3-(1-methylpyrazol-4-ylpropyloxycarbonyl)-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-quinoline,3-(1-phenylpyrazol-4-yl-propyloxycarbonyl)-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-quinolineand pyrazol-1-yl-ethyl2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)-5-methyl-nicotinate.7. A herbicidal and plant growth regulating composition which contains,as active ingredient, an effective amount of a heterocyclylalkyl esterof a 2-imidazolinonenicotinic acid according to claim 1, together withinert carriers and/or other adjuvants.
 8. A method of selectivelycontrolling weeds pre- or postemergence in crops of useful plants, whichmethod comprises treating said useful plants or the crop areas thereofwith an effective amount of a compound according to claim 1, or of acomposition containing such a compound.
 9. A method of inhibiting andsuppressing plant growth beyond the 2-leaf stage, which method comprisestreating the plants during their growth with an effective amount of acompound according to claim 1, or of a composition containing such acompound.
 10. A method of dessicating and defoliating crops of cottonand potatoes to facilitate the harvesting thereof, which methodcomprises treating the crop, shortly before harvesting, with aneffective amount of a compound according to claim 1, or of a compositioncontaining such a compound.